Abstract: A process for obtaining Ketone of formula 1a,b, which includes contacting a Ketone represented by formula 2a,b with a first catalyst under conditions and for a time sufficient to obtain an intermediate mixture, which intermediate mixture contains a Ketone represented by formula 4a,b; and contacting the intermediate mixture, or a fraction thereof, with a second catalyst under conditions effective to provide a product containing a Ketone of formula 1a,b. Moreover, the first catalyst preferably differs from the second catalyst with the first catalyst preferably being an isomerization catalyst and the second catalyst being a cyclization catalyst. The process is capable of providing unexpectedly incresased yields of both Ketone 4 and Ketone 1.

Abstract: Acid catalyzed cyclization of Diels-Alder adducts of myrcene is performed in the presence of hydroxyl-containing compounds, giving the resulting mixtures of isomeric acyloctahydronaphthalenes enhanced quantities of isomers that are particularly useful in perfumery because of their woody-amber odors with enhanced amber note.

Abstract: There is provided a tackifier composition especially suited for use with natural rubber latex and formed from an olefin resin, preferably a polymerized terpene hydrocarbon resin condensed with an unsaturated carboxylic acid or anhydride, optionally partially esterified with a C.sub.1 -C.sub.30 alcohol or phenol, and neutralized with a base, preferably a volatile base such as an amine, and then dispersed in an aqueous medium. The tackifier when added to a latex forms compositions useful particularly as pressure sensitive adhesives.

Abstract: There is provided a process for the addition of a secondary aliphatic amine to myrcene or an 8-substituted myrcene and isomerization to a dialkyl 1,3-dienamine. The process is liquid phase and employs an excess of the amine relative to myrcene or substituted myrcene. The catalyst is an alkali metal amide anion formed from the amine.

Abstract: There is provided an improved process for producing biologically active arylterpenoid compounds useful to inhibit eclosion of pupae, e.g., fly pupae or mosquito pupae. The process is characterized by reacting a terpenoid material having a terminal unsaturated linkage, e.g., dihydromyrcene (3,7-dimethylocta-1,6-diene) with a lower alkyl Grignard reagent, e.g., n-propyl magnesium chloride to form a Grignard exchange product. The exchange product is then benzylated. Either a benzyl halide, e.g., p-isopropylbenzyl chloride, or a benzaldehyde, e.g., p-isopropylbenzaldehyde may be used. These compounds are specifically described in U.S. Pat. No. 4,002,769. They contain also a lower alkoxy group, e.g., methoxy. This can be introduced prior to the formation of the Grignard exchange product or at a later stage in the operation. Use of the exchange-type Grignard reaction enables elimination of several steps when producing the arylterpenoids from pinene as the terpene source, and consequent costs.

Abstract: A process for producing (+)-cis-homocaronic acid from 2-caren-4-ol, 2-caren-4-one, 3-caren-2-ol, or mixtures thereof is disclosed. The reactants are ozonized, the ozonides produced are treated with an oxidizing agent, and the (+)-cis-homocaronic acid is recovered. The oxidizing agent can be hydrogen peroxide in either a basic or an acid medium.

Abstract: Cis- and trans-limonene oxides can be separated effectively one from the other by either fractional distillation or by substantially selectively rearranging with acid catalysis at mild temperature said cis-isomer into trans-dihydrocarvone. The distillatively-separated limonene oxide isomers or the remaining unreacted trans-limonene oxide isomer then is available for discrete conversion into a corresponding dihydrocarvone isomer with minimal equilibration by further acid-catalyzed rearranging at mild temperature.

Abstract: Disclosed is a process for the coupling of a Grignard reagent RMgX with an allylic halide in the presence of a dipolar aprotic solvent wherein the improvement, for obtaining improved yield and selectivity, comprises adding a catalyst to said Grignard or allylic halide and then carrying out the coupling reaction by the addition on the Grignard reagent to the allylic halide, said reaction being characterized by the displacement at the gamma position (relative to the halide) of the allylic halide with R of the Grignard reagent, migration of the allylic double bond in the direction of the halogen atom and loss of halogen. The present invention also resides in the discovery of certain novel procedures for the synthesis of Vitamin E. Specific embodiments of this aspect of the invention reside in the syntheses of 6,7-dehydrophytol, 10,11-dihydrofarnesene, phytone, hexahydropseudoionone, and related compounds as precursors for Vitamin E.

Abstract: Disclosed is a process for the coupling of a Grignard reagent RMgX with an allylic halide in the presence of a dipolar aprotic solvent wherein the improvement, for obtaining improved yield and selectivity, comprises adding a catalyst to said Grignard or allylic halide and then carrying out the coupling reaction by the addition of the Grignard reagent to the allylic halide, said reaction being characterized by the displacement at the gamma position (relative to the halide) of the allylic halide with R of the Grignard reagent, migration of the allylic double bond in the direction of the halogen atom and loss of halogen. The present invention also resides in the discovery of certain novel procedures for the synthesis of Vitamin E. Specific embodiments of this aspect of the invention reside in the syntheses of 6,7-dehydrophytol, 10,11-dihydrofarnesene, phytone, hexahydropseudoionone, and related compounds as precursors for Vitamin E.

Abstract: Disclosed is a process for the coupling of a Grignard reagent RMgX with an allylic halide in the presence of a dipolar aprotic solvent wherein the improvement, for obtaining improved yield and selectivity, comprises adding a catalyst to said Grignard or allylic halide and then carrying out the coupling reaction by the addition of the Grignard reagent to the allylic halide, said reaction being characterized by the displacement at the gamma position (relative to the halide) of the allylic halide with R of the Grignard reagent, migration of the allylic double bond in the direction of the halogen atom and loss of halogen. The present invention also resides in the discovery of certain novel procedures for the synthesis of Vitamin E. Specific embodiments of this aspect of the invention reside in the syntheses of 6,7-dehydrophytol, 10,11-dihydrofarnesene, phytone, hexahydropseudoionone, and related compounds as precursors for Vitamin E.

Abstract: d-3-Menthene of high optical purity is obtained by the selective isomerization/hydrogenation of d-isolimonene in the presence of minor amounts of a palladium catalyst at temperatures up to 200.degree. C. and pressures of preferably about 100-500 psig.

Abstract: Disclosed is a process for the coupling of a Grignard reagent RMgX with an allylic halide in the presence of a dipolar aprotic solvent wherein the improvement, for obtaining improved yield and selectivity, comprises adding a catalyst to said Grignard or allylic halide and then carrying out the coupling reaction by the addition of the Grignard reagent to the allylic halide, said reaction being characterized by the displacement at the gamma position (relative to the halide) of the allylic halide with R of the Grignard reagent, migration of the allylic double bond in the direction of the halogen atom and loss of halogen. The present invention also resides in the discovery of certain novel procedures for the synthesis of Vitamin E. Specific embodiments of this aspect of the invention reside in the syntheses of 6,7-dehydrophytol, 10,11-dihydrofarnesene, phytone, hexahydropseudoionone, and related compounds as precursors for Vitamin E.

Abstract: Disclosed is a process for the coupling of a Grignard reagent RMgX with an allylic halide in the presence of a dipolar aprotic solvent wherein the improvement, for obtaining improved yield and selectivity, comprises adding a catalyst to said Grignard or allylic halide and then carrying out the coupling reaction by the addition of the Grignard reagent to the allylic halide, said reaction being characterized by the displacement at the gamma position (relative to the halide) of the allylic halide with R of the Grignard reagent, migration of the allylic double bond in the direction of the halogen atom and loss of halogen. The present invention also resides in the discovery of certain novel procedures for the synthesis of Vitamin E. Specific embodiments of this aspect of the invention reside in the syntheses of 6,7-dehydrophytol, 10,11-dihydrofarnesene, phytone, hexahydropseudoionone, and related compounds as precursors for Vitamin E.

Abstract: Non-conjugated para-menthadienes having one site of unsaturation at the 4(8)- or 8-position are hydrogenated to selectively form 3-menthene in the presence of a homogeneous ruthenium catalyst complex.

Abstract: New dehydrotocopherols, namely cis- and trans- 3',4'-dehydrotocopherol; cis- and trans- 4',5'-dehydrotocopherol; and 4',4'-a-dehydrotocopherol, and new didehydrotocopherols, namely cis- and trans- 3',4'-11',12'-didehydrotocopherol; cis- and trans- 4',5'-11',12'-didehydrotocopherol; and 4',4'a-11',12'-didehydrotocopherol, are useful intermediates in the preparation of Vitamin E.These intermediates are prepared by reacting trimethylhydroquinone under acid catalysis with certain C.sub.20 intermediates, namely: ##STR1## where R represnts a 3,7-dimethyloctyl or a 3,7-dimethyl-6-octenyl radical and X is halogen, hydroxyl, acetate, C.sub.1-4 alkanoate, C.sub.3-4 alkenoate, aralkenoate and benzoate.

Abstract: A process for the synthesis of 1,4-haloallylic esters from conjugated dienes which comprises preparing a reaction mixture of the conjugated diene, a halogenating agent, and a carboxylic acid and then adding to said reaction mixture a catalytic amount of a strong acid having a high dissociation constant. The invention is particularly described with reference to the synthesis of isoprene-1,4-chloroacetate(1-chloro-4-acetoxy-2-methyl-2-butene) from isoprene wherein a reaction mixture is prepared of isoprene with t-butyl hypochlorite in excess glacial acetic acid, to which is added H.sub.2 SO.sub.4 followed by stirring at 50.degree. C.

Abstract: A process for the preparation of 4-halo-3-methylbut-2-enyl lower fatty acid esters from isoprene comprising the steps of halogenating isoprene in the presence of a dipolar aprotic solvent to produce a reaction mixture of which a predominant portion is 1,4-dihalo-2-methyl-2-butene, and esterifying said dihalo-butene under esterification reaction conditions with an alkali metal salt of a lower fatty acid. The amount of alkali metal salt is sufficient stoichiometrically to replace the halogen ion in the 1-position with the anion of said alkali metal salt, a substantial portion of the product of the esterification reaction being desired 4-halo-3-methylbut-2-enyl lower fatty acid ester.

Abstract: In the process for halogenation of conjugated dienes with elemental halogen under halogenation conditions, the improvement for obtaining increased yield of dihalogenated butene products comprising forming the reaction mixture with a dipolar aprotic solvent vehicle resistant to halogenation under such conditions in the proportion of about 0.05-10 moles per mole of said diene. The invention has particular application in the chlorination of isoprene to 1,4-dichloro-2-methyl-2-butene and 1,2-dichloro-2-methyl-3-butene.